Synthesis of Aspidodispermine via Pericyclic Framework Reconstruction

A divergent approach to the pyrroloquinoline scaffold as present in the class of Aspidosperma alkaloids was developed. As a case study, abundant and renewable nicotinic acid was transformed via pericyclic framework reconstruction into aspidodispermine, a unique member of pyrroloquinoline alkaloids....

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Veröffentlicht in:Organic letters 2020-05, Vol.22 (10), p.3956-3959
Hauptverfasser: Reuß, Franziska, Heretsch, Philipp
Format: Artikel
Sprache:eng
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Zusammenfassung:A divergent approach to the pyrroloquinoline scaffold as present in the class of Aspidosperma alkaloids was developed. As a case study, abundant and renewable nicotinic acid was transformed via pericyclic framework reconstruction into aspidodispermine, a unique member of pyrroloquinoline alkaloids. The sequence comprises a [2 + 2]-photocycloaddition, a Ramberg–Bäcklund contraction, and a strain-promoted formal electrocyclic rearrangement of a bicyclo[2.2.0]­hexene and is potentially extendable to pyrroloindole scaffolds as present in the ibophyllidine alkaloids.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01242